Prostaglandin H2

Prostaglandin H2

Names
Other names PGH2, Endoperoxide H2, Prostaglandin R2
Identifiers
CAS Number	42935-17-1 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15554 Y
ChemSpider	392800 Y
IUPHAR/BPS	4483
MeSH	Prostaglandin+H2
PubChem CID	445049
InChI InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 Y Key: YIBNHAJFJUQSRA-YNNPMVKQSA-N Y InChI=1/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 Key: YIBNHAJFJUQSRA-YNNPMVKQBN
SMILES O=C(O)CCC/C=C\C[C@H]2[C@H]1OO[C@H](C1)[C@@H]2/C=C/[C@@H](O)CCCCC
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
Density	1.129 ± 40.0 g/mL
Boiling point	490 ± 40.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Prostaglandin H2 is a type of prostaglandin and a precursor for many other biologically significant molecules. It is synthesized from arachidonic acid in a reaction catalyzed by a cyclooxygenase enzyme.^[1]

Eicosanoid synthesis - prostaglandin H2 near center

It is acted upon by:

• Prostacyclin synthase to create prostacyclin
• Thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid)
• Prostaglandin D2 synthase to create prostaglandin D2
• Prostaglandin E synthase to create prostaglandin E2

It rearranges non-enzymatically to:

• A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid)

Use of Prostaglandin H2:

• regulating the constriction and dilation of blood vessels
• stimulating platelet aggregation

Effects of Aspirin on Prostaglandin H2:

• Aspirin has been hypothesized to block the conversion of arachidonic acid to Prostaglandin

Figure 1: Synthetic pathways from PGH₂ (the parent compound) to prostaglandins, prostacyclin and thromboxanes

References

2. "Prostaglandin H2". SciFinder. Retrieved 22 October 2017.

3. "Acetylation of Prostaglandin H2 Synthases by Aspirin is Inhibited by Redox Cycling of the Peroxidase". "Biochem Pharmacol. Retrieved 22 October 2017.